US8828392B2 - Histone deacetylase (HDAC) inhibitors (PXD101) for the treatment of cancer alone or in combination with chemotherapeutic agent - Google Patents
Histone deacetylase (HDAC) inhibitors (PXD101) for the treatment of cancer alone or in combination with chemotherapeutic agent Download PDFInfo
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- US8828392B2 US8828392B2 US12/093,069 US9306906A US8828392B2 US 8828392 B2 US8828392 B2 US 8828392B2 US 9306906 A US9306906 A US 9306906A US 8828392 B2 US8828392 B2 US 8828392B2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/65—Tetracyclines
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/69—Boron compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
- A61K39/39533—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals
- A61K39/3955—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals against proteinaceous materials, e.g. enzymes, hormones, lymphokines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Abstract
Description
-
- A is an unsubstituted phenyl group;
- Q1 is a covalent bond, a C1-7alkylene group, or a C2-7alkenylene group;
- J is:
-
- R1 is hydrogen, C1-7alkyl, C3-20heterocyclyl, C5-20aryl, or C5-20aryl-C1-7alkyl; and,
- Q2 is:
-
- mitotic inhibitors, for example vinblastine;
- alkylating agents, for example cisplatin, carboplatin and cyclophosphamide;
- inhibitors of microtubule assembly, like paclitaxel or other taxanes;
- antimetabolites, for example 5-fluorouracil, capecitabine, cytosine arabinoside and hydroxyurea, or, for example, intercalating antibiotics, for example adriamycin and bleomycin;
- immunomodulators, such as lenalidomide (CC-5013/REVLIMID™ (lenalidomide));
- immunostimulants, for example trastuzumab;
- DNA synthesis inhibitors, e.g. gemcitabine;
- enzymes, for example asparaginase;
- topoisomerase inhibitors, for example etoposide;
- proteasome inhibitors, such as bortezomib;
- biological response modifiers, for example interferon;
- corticosteroids, such as dexamethasone and anti-hormones, for example antioestrogens such as tamoxifen and antiandrogens such as (4′-cyano-3-(4-fluorophenylsulphonyl)-2-hydroxy-2-methyl-3′-(trifluoromethyl)-propionanilide;
- antibodies, for example, AVASTIN® (bevacizumab) and rituximab;
- or other therapeutic agents and principles as described in, for example, DeVita, V. T., Jr., Hellmann, S., Rosenberg, S. A.; In: Cancer: Principles & Practice of Oncology, δ.sup.th ed., Lippincott-Raven Publishers (1997).
-
- (a) a histone deacetylase (HDAC) inhibitor, such as PXD-101, preferably as a component of a pharmaceutically acceptable formulation, and preferably provided in a suitable container and/or with suitable packaging; and
- (b) another chemotherapeutic agent, preferably as a component of a pharmaceutically acceptable formulation, and preferably provided in a suitable container and/or with suitable packaging;
- wherein said kit or kit-of-parts is suitable for use in a method for treating cancer.
% activity={(S c −B)/(S°−B)}×100
wherein Sc denotes signal measured in the presence of the compound being tested, S° denotes signal measured in the absence of the compound being tested, and B denotes the background signal measured in blank wells containing medium only. The IC50 corresponds to the drug concentration which achieves 50% activity of untreated control cultures. IC50 values were calculated using the software package Prism 3.0 (GraphPad Software Inc., San Diego, Calif.) with variable slope option.
TABLE 1 | ||
Cell Line | Cell Line Details | PXD-101 IC50 (μM) |
RPMI-8226 | Multiple myeloma | 0.196 |
U266 | Multiple myeloma | 0.141 |
EJM | Multiple myeloma | 0.123 |
LP-1 | MM; t(4; 14)(p16; q32) | 0.045 |
OPM-2 | MM; t(4; 14)(p16; q32) | 0.106 |
KMS-12-BM | MM; t(11; 14)(q13; q32) | 0.088 |
AMO-1 | Plasmacytoma | 0.029 |
L-363 | Plasma cell leukemia | 0.1 |
SK-MM-2 | Plasma cell leukemia | 0.028 |
t(11; 14)(q13; q32) | ||
KARPAS-620 | Plasma cell leukemia | 0.112 |
t(8; 14)(q24; q32) | ||
Mean | 0.097 | |
% activity={(S c −B)/(S°−B)}×100
wherein Sc denotes signal measured in the presence of the compound being tested, S° denotes signal measured in the absence of the compound being tested, and B denotes the background signal measured in blank wells containing medium only. The IC50 corresponds to the concentration which achieves 50% activity. IC50 values were calculated using the software package Prism 3.0 (GraphPad Software Inc., San Diego, Calif.), setting top value at 100 and bottom value at 0.
TABLE 2 |
Summary of Myeloma Combination Studies with PXD-101 in vitro |
PXD-101 combined with: |
Cell Line | Vincristine | Doxorubicin | Melphalan | Dexamethasone |
JJN3 | −(1), +(2), ++(3) | +(1), −(2, 3) | +(1, 2), ++(3) | −(2) |
LP-1 | −(2), +(1, 3) | ++(1), −(2, 3) | −(1, 3), +(2) | ++(1, 2), +++(3) |
RPMI-8226 | ++(1), −(2, 3) | +(1, 2), ++(3) | +(1, 2), ++(3) | +(2) |
U266 | +(1), −(2, 3) | ++(1), +(2), −(3) | +(1, 3), ++(2) | +++(2), ++(3) |
Notes for Table: | ||||
Numbers in brackets is a guide to the schedule used in each experiment (see below). | ||||
Results in Table are those produced using “standard” combination protocol. | ||||
(1) 48 hour co-incubations. | ||||
(2) 24 hour PXD-101 then 48 hour PXD-101 & compound. | ||||
(3) 24 hour compound then 48 hour PXD-101 & compound. |
+++ | Very synergistic | CI <0.3 | ||
++ | Synergistic | CI 0.3-0.7 | ||
+ | Additive | CI 0.7-1 | ||
− | Antagonistic | CI >1 | ||
nd | Not done | |||
PXD-101+Rituximab
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/093,069 US8828392B2 (en) | 2005-11-10 | 2006-11-10 | Histone deacetylase (HDAC) inhibitors (PXD101) for the treatment of cancer alone or in combination with chemotherapeutic agent |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US73570105P | 2005-11-10 | 2005-11-10 | |
US12/093,069 US8828392B2 (en) | 2005-11-10 | 2006-11-10 | Histone deacetylase (HDAC) inhibitors (PXD101) for the treatment of cancer alone or in combination with chemotherapeutic agent |
PCT/GB2006/004215 WO2007054719A2 (en) | 2005-11-10 | 2006-11-10 | Histone deacetylase (hdac) inhibitors (pxdlol) for the treatment of cancer alone or in combination with chemotherapeutic agent |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2006/004215 A-371-Of-International WO2007054719A2 (en) | 2005-11-10 | 2006-11-10 | Histone deacetylase (hdac) inhibitors (pxdlol) for the treatment of cancer alone or in combination with chemotherapeutic agent |
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US14/453,961 Division US9603926B2 (en) | 2005-11-10 | 2014-08-07 | Histone deacetylase (HDAC) inhibitors for the treatment of cancer |
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Publication Number | Publication Date |
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US20080274120A1 US20080274120A1 (en) | 2008-11-06 |
US8828392B2 true US8828392B2 (en) | 2014-09-09 |
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Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/093,069 Active US8828392B2 (en) | 2005-11-10 | 2006-11-10 | Histone deacetylase (HDAC) inhibitors (PXD101) for the treatment of cancer alone or in combination with chemotherapeutic agent |
US14/453,961 Active US9603926B2 (en) | 2005-11-10 | 2014-08-07 | Histone deacetylase (HDAC) inhibitors for the treatment of cancer |
US15/449,151 Active US9980957B2 (en) | 2005-11-10 | 2017-03-03 | Histone deacetylase (HDAC) inhibitors for the treatment of cancer |
US15/989,871 Abandoned US20180271852A1 (en) | 2005-11-10 | 2018-05-25 | Histone Deacetylase (hdac) Inhibitors For The Treatment Of Cancer |
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Application Number | Title | Priority Date | Filing Date |
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US14/453,961 Active US9603926B2 (en) | 2005-11-10 | 2014-08-07 | Histone deacetylase (HDAC) inhibitors for the treatment of cancer |
US15/449,151 Active US9980957B2 (en) | 2005-11-10 | 2017-03-03 | Histone deacetylase (HDAC) inhibitors for the treatment of cancer |
US15/989,871 Abandoned US20180271852A1 (en) | 2005-11-10 | 2018-05-25 | Histone Deacetylase (hdac) Inhibitors For The Treatment Of Cancer |
Country Status (6)
Country | Link |
---|---|
US (4) | US8828392B2 (en) |
EP (2) | EP1957056A2 (en) |
JP (3) | JP5377968B2 (en) |
AU (1) | AU2006313517B2 (en) |
CA (1) | CA2627923C (en) |
WO (1) | WO2007054719A2 (en) |
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US10143697B2 (en) | 2011-03-21 | 2018-12-04 | Valcuria Ab | Pharmaceutic composition comprising of HDAC inhibitor and a steroid and the use thereof |
USRE49240E1 (en) * | 2013-11-05 | 2022-10-11 | The General Hospital Corporation | Inhibitors of histone deacetylase |
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EP2500063A1 (en) | 2005-02-03 | 2012-09-19 | TopoTarget UK Limited | Combination therapy using HDAC inhibitors and melphalan for treating cancer |
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EP1957056A2 (en) | 2005-11-10 | 2008-08-20 | TopoTarget UK Limited | Histone deacetylase (hdac) inhibitors (pxdlol) for the treatment of cancer alone or in combination with chemotherapeutic agent |
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US20180271852A1 (en) | 2018-09-27 |
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US9603926B2 (en) | 2017-03-28 |
WO2007054719A3 (en) | 2007-07-12 |
AU2006313517B2 (en) | 2013-06-27 |
JP2013231063A (en) | 2013-11-14 |
US20140348823A1 (en) | 2014-11-27 |
CA2627923C (en) | 2016-01-12 |
JP2009515861A (en) | 2009-04-16 |
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JP2013049706A (en) | 2013-03-14 |
AU2006313517A1 (en) | 2007-05-18 |
EP2361619A1 (en) | 2011-08-31 |
WO2007054719A2 (en) | 2007-05-18 |
AU2006313517A8 (en) | 2008-06-05 |
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US9980957B2 (en) | 2018-05-29 |
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